Herding Squirrels Episode 17: Rosemary Sanchez on Leadership, Team Mergers, and Thriving Through Chaos
Rosemary Sanchez brings over seven years of leadership experience from a strong technical background, managing both remote and co-located teams through various stages of growth. In this conversation, she shares the story of successfully merging two engineering teams, navigating a high-stakes product launch under time pressure, and the leadership lessons learned from experiencing both her best and worst team experiences. Rosemary offers practical wisdom on building psychological safety, managing uncertainty during organizational change, and why “thrashing” - expending energy without direction - might be the biggest hidden threat to team effectiveness. Her insights on transparency, leveraging diverse perspectives, and using AI tools to challenge leadership blind spots provide a fresh perspective on modern engineering leadership.
Timestamps
00:00 - 02:26 Introduction and personal foundation Rosemary builds her story of growing up with immigrant parents from the Philippines, how her family’s foundation of education and kindness shaped her values, and the symbols she uses to represent love, accomplishment, adversity, and wonder.
02:27 - 06:46 Best team experience: Merging two teams The story of merging two engineering teams with different cultures and ceremonies into one cohesive unit, culminating in a risky visual design system overhaul that touched every UI element in a live product with thousands of users.
06:47 - 09:22 The anatomy of team success How intentional social activities, celebrating small wins, and building comfort with uncertainty created the foundation for the team to handle high-pressure moments without needing orchestration from leadership.
09:23 - 13:17 Worst team experience: Silos and micromanagement The challenges of joining a team with siloed departments, lack of psychological safety, and a culture where information was hoarded rather than shared, leading to distrust and defensive behavior.
13:18 - 16:59 Navigating organizational change and uncertainty Practical strategies for managing through reorgs, restructures, and uncertainty - including knowing when to have conversations, protecting team focus, and avoiding “thrashing.”
17:00 - 20:28 State of thrash and using AI as a leadership tool Defining the concept of “thrashing” - expending energy without direction - and how AI can help leaders tap into anonymous wisdom, challenge biases, and find blind spots when working with confidential information.
20:29 - 23:46 Leadership advice and closing thoughts Rosemary’s model of leadership for new ICs: embrace the wobbly feeling, lean on diverse perspectives, practice transparency, share both successes and struggles, and recognize that adversity might be a friend in disguise.
Key Quotes
On team success: “I didn’t need to orchestrate anything. The team knew who could handle what. People were quick and efficient, and they just cared about each other in that moment. We didn’t want to let each other down.”
On the danger of silos: “When you silo teams and they don’t have information, it creates this mistrust where they think, ‘well, I don’t really want to help this other team because I don’t trust them or I don’t really know what they’re working on.’”
On leadership during uncertainty: “You leaning in and just being a shoulder to help with those emotions and understand like, hey, this is one data point, we don’t know what’s going to happen, but I will be here for you, I think is very important.”
On thrashing: “It’s like when you’re just trying to tread water and you’re thrashing water around. You’re not using that same energy to like, I’m going to swim in that direction. You’re just expending energy, getting nowhere and just patting yourself on the back for staying afloat.”
On leadership for new leaders: “Leadership is going to feel wobbly at first. Lean on diversity and other people’s perspectives to help you along the way. No matter where you go, keep climbing, letting people in to your successes and your sad moments will feel uncomfortable, but it will tap in a level of empathy and more understanding.”
Connect with Rosemary
Find Rosemary on LinkedIn - she’s an introvert who keeps a low social media profile but will probably reply to your message.
